Page last updated: 2024-12-11

2',4',6'-trihydroxychalcone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

pinocembrin chalcone: isolated from Helichrysum trilineatum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

pinocembrin chalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2', 4' and 6' respectively. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6474295
CHEMBL ID129371
CHEBI ID80484
SCHEMBL ID675431
MeSH IDM0301605

Synonyms (29)

Synonym
2'',4'',6''-trihydroxychalcone
(e)-3-phenyl-1-(2,4,6-trihydroxy-phenyl)-propenone
bdbm50042976
3-phenyl-1-(2,4,6-trihydroxy-phenyl)-propenone
BSPBIO_001710
NCGC00179067-01
2',4',6'-trihydroxychalcone
(e)-3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
pinocembrin chalcone
SPECTRUM5_001768
LMPK12120243
3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
CHEMBL129371 ,
chebi:80484 ,
4197-97-1
2-propen-1-one, 3-phenyl-1-(2,4,6-trihydroxyphenyl)-, (e)-
82451-30-7
SCHEMBL675431
(2e)-3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
2;,4;,6;-trihydroxychalcone
pinocembrinchalcone
Q27149535
HY-N7515
CS-0131122
MS-23608
246trihydroxychalcone
E80735
DTXSID101343555
AKOS040760636
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antifungal agentAn antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
chalconesA ketone that is 1,3-diphenylpropenone (benzylideneacetophenone), ArCH=CH(=O)Ar, and its derivatives formed by substitution.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
Flavonoid Biosynthesis1150
pinobanksin biosynthesis115
pinobanksin biosynthesis215

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)120.00000.03403.987110.0000AID293950
Polyunsaturated fatty acid 5-lipoxygenaseRattus norvegicus (Norway rat)IC50 (µMol)140.00000.00462.018210.0000AID6820
Sodium/glucose cotransporter 1Homo sapiens (human)IC50 (µMol)25.40000.06071.61058.4440AID1436776
Sodium/glucose cotransporter 2Homo sapiens (human)IC50 (µMol)33.30000.00050.16534.1000AID1436777
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
chloride transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
glucose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
alpha-glucoside transportSodium/glucose cotransporter 1Homo sapiens (human)
intestinal D-glucose absorptionSodium/glucose cotransporter 1Homo sapiens (human)
response to inorganic substanceSodium/glucose cotransporter 1Homo sapiens (human)
pentose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
fucose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
galactose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
myo-inositol transportSodium/glucose cotransporter 1Homo sapiens (human)
transepithelial water transportSodium/glucose cotransporter 1Homo sapiens (human)
renal glucose absorptionSodium/glucose cotransporter 1Homo sapiens (human)
glucose import across plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
sodium ion import across plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
intestinal hexose absorptionSodium/glucose cotransporter 1Homo sapiens (human)
transport across blood-brain barrierSodium/glucose cotransporter 1Homo sapiens (human)
glucose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
sodium ion transportSodium/glucose cotransporter 1Homo sapiens (human)
alpha-glucoside transportSodium/glucose cotransporter 2Homo sapiens (human)
carbohydrate metabolic processSodium/glucose cotransporter 2Homo sapiens (human)
hexose transmembrane transportSodium/glucose cotransporter 2Homo sapiens (human)
renal glucose absorptionSodium/glucose cotransporter 2Homo sapiens (human)
glucose import across plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
sodium ion import across plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
sodium ion transportSodium/glucose cotransporter 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
galactose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
glucose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
myo-inositol:sodium symporter activitySodium/glucose cotransporter 1Homo sapiens (human)
water transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
glucose:sodium symporter activitySodium/glucose cotransporter 1Homo sapiens (human)
protein bindingSodium/glucose cotransporter 1Homo sapiens (human)
pentose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
fucose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
alpha-glucoside transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
galactose:sodium symporter activitySodium/glucose cotransporter 1Homo sapiens (human)
D-glucose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
low-affinity glucose:sodium symporter activitySodium/glucose cotransporter 2Homo sapiens (human)
glucose:sodium symporter activitySodium/glucose cotransporter 2Homo sapiens (human)
protein bindingSodium/glucose cotransporter 2Homo sapiens (human)
alpha-glucoside transmembrane transporter activitySodium/glucose cotransporter 2Homo sapiens (human)
D-glucose transmembrane transporter activitySodium/glucose cotransporter 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
early endosomeSodium/glucose cotransporter 1Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
apical plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
brush border membraneSodium/glucose cotransporter 1Homo sapiens (human)
intracellular organelleSodium/glucose cotransporter 1Homo sapiens (human)
perinuclear region of cytoplasmSodium/glucose cotransporter 1Homo sapiens (human)
extracellular exosomeSodium/glucose cotransporter 1Homo sapiens (human)
intracellular vesicleSodium/glucose cotransporter 1Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
membraneSodium/glucose cotransporter 2Homo sapiens (human)
apical plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
extracellular exosomeSodium/glucose cotransporter 2Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID161174Inhibition of Prostaglandin G/H synthase activity in sheep seminal vesicle was determined1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors.
AID150737The dissociation constant was measured as binding affinity to P-Glycoprotein C-terminal cytosolic domain using the grafit program.1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Halogenated chalcones with high-affinity binding to P-glycoprotein: potential modulators of multidrug resistance.
AID310794Antibacterial activity against Staphylococcus aureus2007European journal of medicinal chemistry, Feb, Volume: 42, Issue:2
A review of anti-infective and anti-inflammatory chalcones.
AID1436774Cytotoxicity in HEK293 cells assessed as cell viability at 100 uM measured after 20 to 24 hrs by Cell-Titer Blue fluorescence assay2017Journal of medicinal chemistry, 01-26, Volume: 60, Issue:2
Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation.
AID293950Inhibition of mushroom tyrosinase2007Bioorganic & medicinal chemistry, Mar-15, Volume: 15, Issue:6
Synthesis and evaluation of 2',4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors.
AID1436783Inhibition of GLUT in HEK293 cells assessed as reduction in 2-deoxyglucose uptake at 100 uM pretreated for 10 mins followed by 2-deoxyglucose addition in presence of choline buffer measured after 1 hr by resazurin dye based fluorescence assay2017Journal of medicinal chemistry, 01-26, Volume: 60, Issue:2
Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation.
AID1436779Inhibition of human SGLT2 expressed in HEK293 cells assessed as reduction in 2-deoxyglucose uptake at 100 uM pretreated for 10 mins followed by 2-deoxyglucose addition in presence of sodium buffer measured after 1 hr by resazurin dye based fluorescence as2017Journal of medicinal chemistry, 01-26, Volume: 60, Issue:2
Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation.
AID183256Inhibition of lipid peroxidation in rat liver microsomes at 1 uM1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors.
AID1436777Inhibition of human SGLT2 expressed in HEK293 cells assessed as reduction in 2-deoxyglucose uptake pretreated for 10 mins followed by 2-deoxyglucose addition in presence of sodium buffer measured after 1 hr by resazurin dye based fluorescence assay2017Journal of medicinal chemistry, 01-26, Volume: 60, Issue:2
Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation.
AID1436780Inhibition of human SGLT1 expressed in HEK293 cells assessed as reduction in 2-deoxyglucose uptake at 100 uM pretreated for 10 mins followed by 2-deoxyglucose addition in presence of sodium buffer measured after 1 hr by resazurin dye based fluorescence as2017Journal of medicinal chemistry, 01-26, Volume: 60, Issue:2
Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation.
AID6820In vitro inhibition against 5-lipoxygenase in RBL-1 cells was determined1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors.
AID226247The maximal fluorescence quenching was determined using the Grafit program.1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Halogenated chalcones with high-affinity binding to P-glycoprotein: potential modulators of multidrug resistance.
AID1436776Inhibition of human SGLT1 expressed in HEK293 cells assessed as reduction in 2-deoxyglucose uptake pretreated for 10 mins followed by 2-deoxyglucose addition in presence of sodium buffer measured after 1 hr by resazurin dye based fluorescence assay2017Journal of medicinal chemistry, 01-26, Volume: 60, Issue:2
Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (27.27)18.2507
2000's2 (18.18)29.6817
2010's6 (54.55)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.40

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.40 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]